


A bet made in heaven ( kind of)

by Accidental_Shipper



Series: A bet made in heaven [1]
Category: Supernatural
Genre: Angel Gabriel (Supernatural), Bakery and Coffee Shop, Bets & Wagers, Dean Winchester and Sam Are Not Related, Demon Sam Winchester, Destiel - Freeform, Doctor Castiel (Supernatural), First Dates, Fluff, Fluff and Humor, Gabriel and Cas Are Not Related, Gay Castiel (Supernatural), Idiots in Love, M/M, Mechanic Dean Winchester, Oblivious Dean Winchester, Or at least not as explicitly as Gabriel but he does care., Probably will add more tags later, Sharing a Bed, Sweet Castiel (Supernatural), Sweet Dean Winchester, Sweet Gabriel (Supernatural), Sweet Sam Winchester
Language: English
Status: Completed
Published: 2020-07-07
Updated: 2020-07-22
Packaged: 2021-03-05 00:41:15
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 7
Words: 12,700
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25125616
Author URL: https://archiveofourown.org/users/Accidental_Shipper/pseuds/Accidental_Shipper
Summary: Both Sam and Gabriel have opposing views on love, to settle the argument, Sam proposes a wager with his angel friend.Gabriel gets to choose the couple while Sam has to create love provoking scenarios to get the couple to fall in love in a week. Whoever loses has to admit they're wrong, which is something both deities do not want to do.Gabriel accepts the demon's wager and commences to pair a hopeless romantic and gay Doctor Cas Novak with a "straighter than a pole" Mechanic Dean Winchester.Let the love story and bet begin.
Relationships: Castiel/Dean Winchester, Gabriel/Sam Winchester
Series: A bet made in heaven [1]
Series URL: https://archiveofourown.org/series/1851085
Comments: 41
Kudos: 97





	1. Chapter 1

The man ran across the streets with a small satchel placed on his chest. He held it tightly as to not drop any of the items hidden inside. His eyes turned to every corner, prepared to lookout for anything that may be hidden within the shadows but, still apprehensive of the possibility that they might jump out.

He caught his breath once he stood at the entrance of an empty alleyway, the darkness of the night quelled any possibility to see beyond the trash cans at the beginning of the long corridor and the man, unable to see what stood in front of him, pulled out a single candle from his satchel and lit it up. Confident that he had found a place to work unnoticed, he took the candlestick to the farthest ends of the alleyway.

Once there, he took the remaining items from his satchel including four more candlesticks, chalk, bowl, and various herbs and skulls from small mammals. All the ingredient needed for the spell. With a shaking hand, he drew a small circle and a star at its center. He lit up the remaining candles sticks and began grinding the herbs together, unaware of the hellhound creeping up behind him.

A loud snarl erupted the silence of the dark-consumed alleyway and the man, who had just placed the bowl at the center of the circle, heard the heavy breathing from behind him. Slowly, he took the knife from the satchel and waited for the hound to approach. Each step from the hound was accompanied by the sound of sharp claws scraping across the stoned pavement. The sound was enough to put other people to a state of terror however, for the man, all it did was provide insight to the distance between him and the beast.

Once the man felt its cold snout upon his ear, he took his knife and rammed it through the hound’s jaw causing the hound to howl in pain and scurry away. The man, convinced that the hound would no longer attack him, turned around to continue the spell.

But, as the man turned to finish his spell, he quickly noticed that the bowl with all the ingredients was gone and all the candlesticks had burned out, except for one which had a pair of black, leather shoes placed between it.

With the dim light that the candlelight could provide, the small flame illuminated a tall figure hovering over the kneeled man.

“tsk, tsk, tsk looks like someone is trying to cheat. I guess you humans never learned how to play fair” said the figure with a devilish grin creeping into its features.

The man felt his entire body trembling in fear. His tongue was frozen, unable to utter any words of forgiveness or reconsideration. The man bowed before the figure in a fleeting attempt to ask it to consider the man’s excuse to act in defiance to the approved accord.

“I just need more time” the man somehow managed to utter.

“I bet you did” said Sam before he summoned another hellhound to drag the man to hell.

When everything was settled, Sam looked down at the contents of the bowl and asked himself: _How did he manage to get the ingredients needed for the spell, let alone know of the spell’s existence?_

However, his question was immediately answered when the sound of wings echoed across the alleyway.

Sam couldn’t help but smile when he heard that familiar sound “Gabriel, I didn’t know you were accustomed to witchcraft?”

“I am not” replied Gabriel “I got the spell from a red-head”.

“Under what deal?” asked Sam.

“Sex” Gabriel didn’t even try to mitigate.

Sam gagged in response. He didn’t want to get into Gabriel’s sex life so, he changed the conversation entirely:

“Why did you give him the spell?”

“To help him”

“Yeah, no shit, but why?”

Gabriel smiled a little bit but, not without a touch of sadness.

“He still needed to confess his love to his sweetheart”.

Sam was taken aback but, not like one would expect. He was appalled by Gabriel’s justification, more appalled than the fact that Gabriel had sex with a witch.

“You’re joking right?” said Sam, half-hoping that Gabriel was.

Gabriel surely didn’t look deceitful “You would understand if you could love”.

“Gabriel” Sam said mockingly “I may be a demon who is incapable of love but, I know how it works”.

“Really?” Gabriel asked judgmentally.

“Yes, all that is required is a five second gaze into each other’s eyes to be romantically intimate and besides”. Sam added “The man had ten years to confess his love”.

“I think it’s more complicated than that” Gabriel smirked, now fully confident on his judgement of Sam and his little understanding of how complicated and time consuming the subject-matter can be. “Sometimes love is a slow burn, Sammy” he added.

“Want to bet on it?” Sam proposed.

Gabriel paused, he knew that Sam only made wagers with the ill-fated, those that Sam knew would ultimately lose. This meant that Sam was fully confident in his conviction, what a shame. Hopefully Gabriel would knock some sense into the handsome demon.

“Sure, what are the rules?”

Sam smiled a devilish grin “You will pair two people of your choosing and I will manipulate the situations of said pairing, I will not manipulate their minds though, only the circumstances they find themselves in. If they don’t fall in love in a week then you win but, if they do, which they will, I win”.

“What is the punishment for the person that loses?”

“A simple apology of: ‘I was wrong’”.

A simple punishment that, no doubt, carried its weight. A punch to a deity’s hubris is not taken lightly, not for a demon or angel. Even so, Gabriel was eager to engage in this little challenge:

“You’re on, demon”.

With that, both deities shook hands and before Sam could react, Gabriel snapped his fingers and suddenly both deities were standing inside a doctor's office.

“Why are we here?” asked Sam.

“Didn’t we just agree that I would choose the pairing?” asked Gabriel with one of his eyebrows lifted upward.

“Right, so who do we have?” Gabriel didn’t respond, instead he pointed his finger towards a man standing in front of a mirror while reading a book titled: _A Hundred Ways to A Man’s Heart._

The man in question cleared his throat before uttering:

“I bet a man like you drinks his milk” He paused for a few seconds before looking down at the book in confusion “Why would I compliment a man for consuming a white liquid produced by cows?” He asked himself before flipping through the pages to find an answer.

“This young gentleman right here Sammy is Cas Novak, a very gay doctor who wants nothing more than to find love but, is unable to do so because of his…” Gabriel paused, trying to find the appropriate, diplomatic term “lack of communication skills” he added.

“What is Cas short for?” asked Sam.

“Casanova”

“No, it’s not” Sam interjected.

“Yeah, I didn’t believe it a first either”.

Before Sam could object, a young nurse came through the door.

“Cas, Mr. Johnson is here” she said.

“Okay Meg bring him over” said Cas hastily, trying his best to hide the book by placing it behind his back.

Meg didn’t seem to care though; she simply left the door open before going to get Cas’ next patient.

Cas quickly pulled out his book and began flipping through the pages again, trying desperately to find the answer to his previously asked question. However, he failed to so as his patient stepped inside.

“Wow, he’s cute” said Gabriel.

“I guess he’s okay” Sam begrudgingly agreed, somehow envious by the fact that Gabriel would find another man attractive.

“Good morning Doctor” said the patient.

“Good morning to you too Mr. Johnson, are you here for your check up?” asked Cas, putting his book upside down on his desk. 

Mr. Johnson nodded.

“Good” replied Cas “Now just take a seat by the table over there and we will begin” he added.

“So far, so good” said Sam.

“Just you wait” Gabriel smirked; arms crossed.

Cas took out his stethoscope and listened to Mr. Johnson’s heart, satisfied that it was at a steadily beat. He nodded in approval before taking out his pen and writing something on his clip board. Things were going good however, both men hadn’t said a single word to each other. And Cas, unable to stand the silence, blurted out:

“I bet a man like you drinks his milk”.

“Uhm no, I am lactose intoler- “

“Because you’re a cow” Cas hastily added.

If there wasn’t silence before, there was now. Sam’s mouth hung wide open while Gabriel massaged his temples.

“Thanks…” replied Johnson.

Cas looked down in shame “Let me just continue the checkup” said Cas, now just completely embarrassed.

“This is just peachy, huh Sammy” said Gabriel. 

“I can make this work” opposed Sam, though not with much confidence in his voice.

“Shall we meet our other player then?” asked Gabriel before snapping his finger and bringing them to a large garage.

In front of them stood a man working on a car. An Impala 67, Sam recognized. The man had oil stains all over his face and was working on the car vigorously, almost as though his life depended on it.

“Aside from loving his car, which he appropriately named ‘Baby’ btw, Dean Winchester here loves women. Trust me, I checked his search history” said Gabriel “I got to hand it to him, it takes a lot of guts to log on to those websites without going on incognito mode” he added.

“Why are you pairing a hopeless romantic, gay Doctor with a ‘straighter than a pole’ mechanic?” asked Sam.

“To make it challenging, duh. And besides” Gabriel added “Since you think that love is so easy, you should create a romantic connection in no time, right?”.

“Right” said Sam, trying to sound all smug.

However, Gabriel wasn’t having any of it:

“Okay then Sam-a-lam, manipulate the situation; create a scenario where these two idiots meet”.

Sam looked around and quickly saw a mop bucket laying close by. Fortunately for him, Dean started walking towards its general direction. With a snap of his fingers, Sam tumbled over the bucket and caused the water to spill and Dean, who was not paying attention, slipped on the water and crashed on his side and hit his arm.

“Son of a bitch!” he yelled before grapping his arm in pain.

“There, with that broken arm he surely needs a Doctor visit, right Gabriel?”

“Right” smirked Gabriel “Let the love story commence”. 


	2. Some drastic measures were taken

Gabriel and Sam sat discretely in the backseats of the Impala whilst Dean drove with only one hand. The other arm was causing such excruciating pain that Dean had to stop every two minutes or so just to try to alleviate it which ultimately never worked as a single touch would only aggravate the pain further.

“Lets just hope that this is the worst thing you do to him” said Gabriel whilst giving Sam a scrutinizing look.

“I wouldn’t need to anyways” replied Sam “Once Dean makes it to the Doctor’s office and sees Cas with those green eyes of his, he will fall instantly in love; claiming me the winner”.

“I thought you said that Dean was ‘straighter than a pole’” Gabriel remarked whilst saying the last bit of the sentence with air quotations.

Sam shrugged “I bet he’s desperate, he looks like someone who didn’t receive a notification on his dating profile for years”.

Gabriel smirked but, not because of Sam’s comment. It was unfortunate that Sam stood firm in his inadequate credence on the nature of love. Gabriel had hoped that it was because of Sam’s desire to retain his status as a cold-hearted demon and not because he truly believed in it. It is hard to explain why Gabriel wanted so desperately to win, when Sam scoffed at Gabriel’s justification to provide the man with the spell, it felt like Sam punched Gabriel in the gut.

Gabriel wanted to win, not because he wanted the glorification but because he hoped that a lesson would be learned when the bet was thru.

“I not sure that even the most desperate man would fall for Cas’ one-liners” Gabriel quipped.

Gabriel had to hold back a laugh when he saw Sam begin to sweat and physically pause in realization.

“Crap, you’re right”

Unfortunately for Sam, he was no longer going to be a mere outside observer to Cas and Dean’s blossoming romance. No longer was he going to make one of them slip to have the other conveniently catch them before they fall. From now on, he was going to be an active participant; conjuring up situations that only screamed a forced romantic kiss. And being the sore player that he was, he was not going to have Cas and Dean’s first meeting be equipped with Cas’ stupid one-liners from a book that he probably got for a cheap price on eBay.

Sam snapped his fingers and once again he and Gabriel were in Cas’ office except, this time, Meg was in the room.

“Why did you call Mr. Johnson a cow?” asked Meg.

Cas was twiddling his thumbs, still embarrassed of the entire situation “I was trying to provide an adequate excuse for my remark addressing his likely indulgence of milk”.

When Meg only gave him a dumbfounded expression, he added “the book told me to compliment his likely indulgence of milk”.

Meg sighed heavily, massaging her temples “Cas, you may be a Doctor but it’s not like you work in the ER where hundreds of patients come in regularly. This is a small-town Cas, sooner or later everybody is going to hear about the local doctor who calls people after various types of livestock. You just can’t afford losing your reputation.”

Cas contemplated this “I will refrain from calling people livestock”.

“Good” replied Meg “Now finish your coffee, you only got 5 minutes left before your next shift”.

Both Sam and Gabriel watched Meg exit the door and Sam managed to release a relieved sigh.

“Well he won’t be using that book anytime soon”.

However, his claim was almost immediately discredited when Cas took a seat behind his desk and started flipping through the pages.

“Maybe I can find something here that does not involve the consumption of liquids”.

Gabriel could practically see the steam emanating from Sam’s head and with a frustrated huff, Sam snapped his fingers and the coffee cup was knocked over and all its contents spilled over Cas’ book.

Cas quickly stood up and slightly panicked at the mess in front of him. He grabbed some paper towels and started wiping away the hot liquid. He placed the coffee cup next to the sink and finally, looked down at his soaked book with the saddest looking pout in existence.

“It’s ruined” Cas frowned.

“Good” said Sam.

“You’re just awful” remarked Gabriel, shaking his head in a mocking expression of disgust.

It didn’t take long then for Dean to arrive at the lobby. Meg took him to Cas’ office without question as a hand grasped around an arm is a clear indicator that the arm was broken.

Meg took Dean inside and stood outside of the doorway. Before she could ask if Cas needed help, Sam promptly slammed the door in front of Meg’s face.

“What is his problem?”.

“What is her problem?”.

Meg and Cas asked simultaneously from two opposite ends of the door. Dean didn’t seem to notice as he let out a loud grunt. Cas, who was now fully alerted by Dean’s distress, pulled up Dean’s short sleeve to examine his arm.

Sam waited in anticipation for the moment of intimacy, for Dean and Cas to lock eyes with each other and fall instantly in love. However, that moment never came as they weren’t even looking at each other. Dean was busy looking absent-mindedly around the office while Cas was closely inspecting Dean’s arm. Sam could only sense Gabriel’s growing smug from six feet below.

“Your arm does not appear to be broken, only your shoulder is dislocated. I can put it back in place, but it will slightly hurt, are you okay with that?” asked Cas.

Dean looked at Cas but, not with the intimacy that Sam had hoped. He looked at Cas with the same expression that anyone would have with a professional, slightly impassive.

Dean shrugged “Whatever I don’t really care”.

With that Cas put his hands in place and relocated the shoulder with ease. Apparently, Dean did care as he responded to the treatment with a loud yell.

“Son of a bitch” he whispered, pitifully.

A small smile crept into Cas’ features; he was slightly amused by Dean’s pitiful display. Despite his broody nature, Cas could tell that Dean had a heart of gold hidden underneath. It was fortunate that only Gabriel saw the smile and not Sam, who was too busy looking at the two men in utter confusion, guess the only display of affection that Sam was accustomed to was long silent glances and the three-word confession.

“Now I would recommend putting ice on the injury and to maintain the range of motion of your shoulder. Your name is Dean Winchester, right? I don’t see you in my medical record” said Cas, looking through his file.

“Oh, that’s because I am new to town” lied Dean.

“That’s not an issue all you have to do is- “

“No, no that’s okay, I am perfectly healthy” interrupted Dean “I eat my vegetables” he jokingly added.

“Bitch please, he will only eat his vegetables if it's between his burgers” Gabriel told Sam.

“So, he doesn’t want to provide Cas a medical record because he knows that Cas would have a heart-attack if he saw it?” asked Sam.

“Bingo”.

“You have been a real help Dr. Novak but, I should be on my way” Dean hastily said, trying to flee before the topic of the medical record came up again.

“It’s not an issue Mr. Winchester, you can contact me if there is any other issue with your shoulder” Cas smiled, politely.

Dean smiled back before exiting the door.

Gabriel stretched his arm out dramatically and said:

“Well that was anti-climactic, I was so sure that the rose petals would start falling once they locked eyes with each other. Oh well, maybe next time right Sammy, Sammy?”.

Gabriel looked around but, Sam was nowhere to be seen. Instead he was following Dean like a shadow, looking around for something to stop him before he left the building entirely. Fortunately, Sam was having a bit of luck with the conveniently placed objects as he saw a marker just laying there on the edge of the lobby’s desk counter. He flipped the marker on the floor with the snap of his fingers and Dean, once again, crashed onto the floor.

“Are you kidding me?” Dean yelled at the top of his lungs. 

“Are you really trying to break every bone on his body?” asked Gabriel after he managed to catch up. 

“It is merely a precaution” replied Sam, sounding slightly annoyed.

Dean luckily didn’t hit his shoulder but, he certainly broke his back. Meg and Cas rushed over and helped Dean up.

“Are you okay Mr. Winchester?” asked Meg concerned.

“I’m okay” Dean annoyingly replied. He lifted himself up from Meg and Cas’ arms and cleared his throat “Well, I will be heading of now. Again, thank you Doctor for your help, but I will be going now”.

“Wait” objected Cas “Let me follow you home so you don’t suffer any more accidents” he offered.

Meg and Dean looked at Cas in confusion. That is a weird offer for a Doctor to make, even from one who would do checkups from their patient’s homes. However, Dean was not one to turn down an offer, especially one that made the trip to the garage slightly safer.

“Okay Dr. Novak, after you” Dean gestured Cas to go past him. Cas went through the front door and Dean quickly followed.

Cas gave the offer to gain a better reputation as a Doctor than what he was gave Mr. Johnson earlier that day. He hoped that Dean would express his gratitude by telling everyone of Cas’ great services. 

As for Gabriel , he could sense Sam’s building frustration since the Doctor visit and was starting to get afraid of Sam taking drastic measures to get the results he wanted, which he would inevitable do.

When Cas and Dean stepped out of their individual cars and walked towards the garage, Dean turned to Cas and said:

“Thank you again, Dr. Novak you provided a great service”.

“You are very welcome Mr. Winchester” said Cas slightly smiling at Dean’s gratitude “Make sure you are more careful” he added.

When Cas and Dean waved each other goodbye, Sam frantically checked for conveniently placed objects for Cas to trip over. When Cas was getting closer to his car and with nothing for him to trip over, Sam panicked and snapped his fingers.

The drastic measure was taken when Cas’ car spontaneously blew up in flames. Cas, Dean, and Gabriel’s mouths hung open when Cas’ car was engulfed in black smoke.

“What the hell, Michael Bay!” yelled Gabriel to Sam.


	3. Finally getting somewhere

Sam was quite arguably one of most vicious demon’s that hell has conjured up. He took no pity for the ill-fated souls that signed his contracts as he saw them as mere pawns to his unfair game of fatal chess.

Gabriel had met Sam when he went down to earth to announce the birth of Jesus to Mary, Sam had proposed a small wager with Gabriel concerning the fate of the man. Sam predicted that he wouldn’t die on the cross whereas Gabriel predicted he would. Of course, Gabriel won as he knew of God’s plan. However, Gabriel felt that Sam knew the outcome as well but purposely lost, which went against Sam’s nature as a demon who always wanted to win.

After that, Sam never proposed a wager against Gabriel which could mean two different things, either Sam is a sore loser, or he managed to come up with an adequate excuse to treat Gabriel as an equal and not another ill-fated pawn for Sam to play with. Gabriel hoped that it was the latter as he enjoyed his time on earth with Sam even if it didn’t quite measure up to the time Gabriel had spent performing his duties in heaven.

Gabriel enjoyed himself when they would simply sit down together and watch humankind from afar. Over time, Gabriel would grow fond of the mortals whereas Sam would retain his distaste, just to keep his title as a professional asshole.

Well, maybe that was a bit wrong; Sam isn't always a professional asshole, there are few occasions when Sam could act like he had a soul. Especially now, sitting on a dining table with his face glued to the floor, his hands under the table, and looking like a scolded child.

“I- “he sighed heavily “I may have overreacted” he finished, not daring to look at Gabriel’s scornful expression.

“You may have?” Gabriel asked sarcastically. 

Cas and Dean drove to a local diner just a few blocks away from Dean’s garage. Dean needed a beer and Cas probably needed two, just in the hopes that he would drop dead as he was someone who couldn’t hold his liquor. Gabriel and Sam followed them and took a seat at the complete opposite end of the diner as they were no longer invisible to the human eye.

“I mean seriously Sam; you are starting to act like a fanatic. But, instead of sending death threats on twitter you're blowing up people's cars”.

Sam was still looking down, but he managed to mutter “I needed them to stay together because the minute one of them leaves it wouldn’t work anymore”.

That took Gabriel by surprise. Honestly, he wasn’t expecting Sam to take the wager so personally. When Sam lost that wager over a millennium ago, all he did was shake hands with Gabriel without any complaints. It was almost as though the topic of the wager was a sensitive one for Sam but, Gabriel didn’t understand why.

“You still have a week, Sam. You have plenty of time” said Gabriel, trying his best to reassure Sam.

Sam looked up at Gabriel and smiled. Before he could say anything though, a waitress came to their seat and asked:

“Anything for you two gentlemen?”.

“Yes please, a regular coffee for me and hot chocolate for my friend over here” Sam told her “Could you add some marshmallows if it's possible” he added.

“Of course, your drinks will come shortly”.

“Thank you” said Sam.

When the waitress left, Gabriel looked at Sam and said:

“Well, that was nice of you”.

Sam merely shrugged “It’s what you always order”.

Over at the opposite end of the diner, Cas and Dean sat silently and waited for their drinks to come. Dean couldn’t help but feel sorry for the man. Never in his ten years of working as a mechanic, did he witness a car spontaneously explode out of nowhere. After he put out the flames with a fire extinguisher, he looked under the car to see if there was bomb hidden underneath. When he saw that there was no bomb, he concluded that there was no one trying to kill the local Doctor.

Cas, for his part, was convinced that someone was pulling his strings. When Dean tried to leave his office, he slipped on a marker and when Cas tried to leave the garage, his car exploded. It was almost as though an unseen force was trying to pull them together, was it an angel? or perhaps even God himself? He wasn’t quite sure but, there was no way he was going to blow this opportunity. He had experienced too many tinder dates to fail now, he was going-

“Cas, you’re getting to close for comfort” said Dean, interrupting Cas' thoughts.

Cas paused and realized that he had lifted himself off his seat and inched his way closer to Dean’s face. Blushing in embarrassment, he sat back down and put his hands underneath the table. When the waitress came with the beers, Cas immediately took his beer and slugged down like it was water.

_Damn, he must be really upset about his car._ Thought Dean, completely oblivious to the entire situation.

“Uhm, Cas…wait, can you call you Cas?” asked Dean.

“I will allow you to address me by my birth name outside of my office” said Cas after finishing his beer and was slightly disappointed by the fact that he didn’t get instantly intoxicated.

“Okay, Cas- actually, what is Cas short for?” Dean asked, curiously. 

“Castiel”

“See, told you his name wasn’t Casanova” said Sam who somehow managed to hear the conversation from ten meters apart.

Gabriel took out his phone and said:

“But it says here Casanova”.

Sam took Gabriel’s phone to look and after a moment let out an annoyed sigh.

“Gabriel, this is his screen name for his dating profile”.

“Yeesh, no wonder the guy never got laid” replied Gabriel.

The waitress came shortly after with their drinks and Gabriel nearly squealed when he got four marshmallows instead of the usual three. It would be a lie if his excitement wasn’t enough to put a smile on the cold-hearted demon’s face. 

“Castiel, wow; that’s really a unique name” Dean complimented.

“Thank you, I got it on my birthday” quipped Cas.

Somewhere on the opposite end of the diner, a loud thud could be heard as Sam slammed his face on the table despite Gabriel’s protests.

“Okay, Cas” said Dean, slightly uncomfortable and wanting to go back to the topic that he initially intended to discuss first “I know this car shop that has great vehicles, it’s a day drive but you should go, considering that you don’t have a car anymore.”

“But how will I get there?” asked Cas.

“I could always drive you” suggested Dean.

Sam, Gabriel, and Cas all physically paused at Dean’s suggestion. Cas stood completely still while Gabriel and Sam looked at each other with their mouths wide open. It appears that only Dean wasn’t aware of the fact that his suggestion implied a date.

“Of course, if your busy then- “

However, Dean was interrupted by Cas when he pulled out his phone and called Meg. He told her to “Bring Jimmy over” which was a code they would use to imply that he was going out and that she needed to take his place for a few days.

“There it’s settled, are we going now?” asked Cas in an alarming speed.

Dean was taken aback by Cas’ quick response. However, he quickly brushed it off and took some dollar bills out of his jeans and placed it on the table.

“Let’s go then” he said.

Gabriel and Sam quickly drank their drinks despite the hot temperature burning their throats and slammed some dollar bills onto the table. They then quickly turned invisible and started following Cas and Dean, unaware of the man who saw them vanish and started to reconsider taking another beer.

Looks like the bet was finally getting somewhere.

**Notes for the Chapter:**

> So, Cas and Dean finally managed to get somewhere. That's fun. 
> 
> The next chapters will consist of Demon!Sam hijinks and some development for our two couples. 
> 
> ( Also fun fact: one bit of dialogue between Dean and Cas is based on an incorrect quote from Tumblr, I don't know I thought it would be funny to incorporate that into the story). 
> 
> Anyways, I hope that you all enjoy what's to come!


	4. Not a typical rom-com scenario

Somewhere in Ancient Greece the playwright Aristophanes, best known for his comedic satire, hosted a dinner party where he told his guests a story concerning the fundamental nature of love.

In the story, it is told that initially humans had four arms, four legs, and two heads but were split in half by Zeus after he deemed them too powerful to exist on earth. 

Once the humans were split from their other halves, the concept of love was introduced as the driving principle motivating people to find their other half and return to their primal state of being whole again.

Of course, Gabriel was too distracted by the fact that humans used to have two heads to notice the implications hidden underneath the story. When he asked God why he didn’t go with that design, he was temporarily kicked out of heaven for “questioning his father’s authority”.

It was not that he had no understanding of the concept of love, in fact, he knew two things, it was just that he really wanted to see two-headed, four-armed, and four-legged humans roam the earth again. But, do not fret, as he managed to create his own abomination in the form of the platypus which God would place in Australia along with the other failed attempts at a functioning species.

Addressing the two things he knew about love; one was that love was a slow burn and the second was that love could not be evoked by listening to a constant repeat of Celine Dion songs through the radio. There is only one song that can constantly be repeated to evoke love, and that is “Heat of the moment” and not “Because you loved me” as Sam so falsely believed.

Sam took it upon himself to mess around with Dean’s radio whilst he was driving to the nearest motel to call it a night before going to the car shop the next day.

Dean kept trying to put a new mix tape in only to have Sam keep taking it out and play another romantic song from Celine Dion. Dean drew the line though when he turned the sound off entirely to resolve the issue, Sam was so offended by this that he responded by blasting the Celine Dion’s song on the loudest volume, resulting in everyone’s eardrums being nearly shattered. It was safe to say that Sam’s response nearly resulted in a car crash however, he felt victorious as Dean just gave up and let “My heart will go on” continue playing.

Fortunately, Gabriel could ignore Sam’s shenanigans by enduring the harassment inflicted by the officials in heaven through constant complaints sent by text messages. Gabriel was too busy sending replies to realize that Sam had played “My heart will go on” for the fifth time.

“What are they complaining about this time?” asked Sam after he realized Gabriel wasn’t laughing with him when Dean groaned in response to having the song repeated for the fifth time.

“They just want to know when I’ll be back” said Gabriel “I told them I would be back in a week after I finish my ‘errands’” he said the last bit whilst doing air quotations with only his left hand.

Gabriel looked back on his phone and Sam could feel his features morphing into a melancholic expression, which he was glad went unnoticed by Gabriel.

“You know, sooner or later one of them is going to jump out of the car because of the horrible repeats” quipped Gabriel.

Sam chuckled to loosen the knot in his throat. Before he could come up with a quippy reply though, he was interrupted by Dean who decided it would be an appropriate time to talk after what felt like an eternity of silence.

“I normally never listen to this type of stuff, I usually listen to the Who’s and sing along” he said awkwardly, obviously not equipped to deal with embarrassing situations. 

Cas thought for a minute before he replied with unexpected enthusiasm “How about we just sing along with Celine?”.

“What?” replied Sam and Dean simultaneously.

However, Cas didn’t answer that question as he began singing the first verse of the song.

Every night in my dreams

I see you, I feel you

That is how I know you go on.

“Are you kidding me?” cringed Sam. He rubbed his face with his hands and grunted. However, his thoughts of vicarious embarrassment were completely discarded when he heard Dean singing along.

Far across the distance

And spaces between us

You have come to show you go on

Before Sam could process what was going along, Gabriel tagged along.

Near, far, wherever you are

I believe that the heart does go on

Once more you open the door

And you're here in my heart

And my heart will go on and on

Gabriel nudged Sam to join in and Sam, not wanting to be left out, complied.

Love can touch us one time

And last for a lifetime

And never let go 'til we're gone

Love was when I loved you

One true time I'd hold to

In my life we'll always go on

Near, far, wherever you are

I believe that the heart does go on

Once more you open the door

And you're here in my heart

And my heart will go on and on

You're here, there's nothing I fear

And I know that my heart will go on

We'll stay forever this way

You are safe in my heart and

My heart will go on and on

In the end everyone was laughing, each couple looked into their partner's eyes and smiled. The awkward tension was eased and now a sense of fondness could be felt within the impala.

Sam snapped his fingers and once again Dean’s mixtape started playing and Dean let out a sigh of relief.

“I guess that did the trick, huh?” he said to Cas jokingly.

Cas smiled softly “I guess it did”.

Shortly thereafter they arrived at the parking lot of the motel. Gabriel turned to Sam and could recognize by his smirk that he was plotting something that only Sam would consider ingenious. Sam watched this trope play in many corny romance movie (which he would never admit watching to Gabriel) and was somehow excited by the fact that he would recreate it for the billionth time.

Sam snapped his fingers and, together with Gabriel, stood in front of the lobby’s desk. Before the receptionist could say anything, Sam transported her to the nearest mop closet and then took on her appearance. He asked Gabriel kindly to join the receptionist in the closet, which Gabriel confusingly complied, before he went to take the receptionist’s place behind the desk.

Cas and Dean came in and Sam took on his best greeting smile, which fortunately looked less horrifying coming from a young girl’s face.

“Good evening, gentlemen” Sam said.

“Good evening” said Dean “We would like to a reserve a room, two queens”.

“Sure thing” Sam winked before passing Dean the key “room 69” Sam grinned.

“Thank you” Dean said before taking Cas to the appointed room.

“I can’t believe I was stuffed in a closet for _this_ ” said the receptionist with her head poking out of the closet.

“Yeah Sammy, I thought you would be more creative” said Gabriel, mimicking the receptionist’s actions.

“Hush” said Sam with the grin still plastered on his face “You two, back in the closet”.

The receptionist rolled her eyes “It’s not like I ever left anyways”.

Cas and Dean walked through the hallway to look for their room. They managed to find it in a bit of an obscure area compared to the other rooms as it did not have another room beside it and had its own small space despite the other rooms being just next each other in one long hallway. Cas nor Dean understood the implication behind this weird arrangement until Dean opened the door and saw what was inside.

A heart shaped bed with rose petals scattered across the bedcovers and a champagne bottle on the nightstand with two glasses placed beside it. The lighting of the room was dark red and slow jazz music could be heard in the background. 

Cas’ face was red from blushing while Dean’s face was an exact replica of the famous painting made by Edvard Munch. With an enraged and embarrassed huff, Dean stormed to the receptionist with murderous intent. 

However, Sam was prepared for Dean’s outburst and waited for him to return just to convey the conversation he had mapped out in his head.

“Can I help you?” asked Sam the minute he saw Dean’s scornful expression.

“Yes, you can” He said, trying to sound polite even though it was obvious that he was upset “I said that I wanted a room with two queens not an erotic chamber for horny couples.”

“Oh” said Sam with a mocking expression of surprise “I thought the words ‘two queens’ was a way to mitigate your embarrassment of coming into a motel specifically for couples”.

“What are you talking about?” questioned Dean.

“You see this motel is specifically for couples who want to” Sam paused with an index finger placed on his chin, indicating that he was thinking of an appropriate term “relieve themselves” he finished.

“That’s not true” said Dean “I have been here on numerous occasions and I got in without needing a significant other”.

“New owner, new policy” replied Sam.

“Listen” said Sam after Dean remained silent “Either you stay in your room or you sleep on the side of road in the middle of nowhere which, judging from your disdainful expression, is something you are not willing to do”.

Sam smirked, confident in his position as the person with the upper hand in the conversation. However, his confidence was shattered when Dean replied:

“Actually, I think I am”.

There was a stunned silence.

“What” Sam said with a demonic voice.

However, before he could inflict some serious damage, he was hit on the head with a shoe.

Dean looked around and managed to see a closet door suddenly shut close.

“Fine” Sam huffed “Close the door and give me the keys when you’re done”.

“Thank you” replied Dean with a smug before going to grab Cas.

Gabriel came out of the closet with the receptionist and grabbed his shoe.

“Hope I won’t get in trouble for this” said the receptionist.

“Don’t worry Charlie” said Gabriel “We will delete any bad review that may come on yelp”.

“Thanks” said Charlie.

Gabriel snapped his fingers and he and Sam were once again placed in the backseat of the impala. Dean and Cas came shortly after and not a single word was uttered through the first five minutes of the drive.

“Gabriel- “.

“Don’t Sam” interrupted Gabriel “After all this time, I thought you would look at humanity a little different. Dean is not like your other pawns, Sam. His judgement is not clouded by heartbreak or sorrow. He is more than capable of overcoming your games. You cannot evoke love by pushing two people together”.

“Like you know so much about love” said Sam.

“A lot more than you apparently” spat Gabriel.

Gabriel turned his head to the window, intent of avoiding Sam’s eyes.

Just then a loud pop could be heard, and everyone paused as the impala was driving a lot slower.

“Shit” cussed Dean.

“What’s wrong?” asked Cas.

“The tire is broken”.

Dean pulled over on the side of the road and exited the car with Cas quickly following.

“You’re just that petty, huh?” said Gabriel.

“It wasn’t me” replied Sam.

Gabriel looked at Sam in confusion before they exited the car and watched Dean take out the essential tools and new tire from the trunk. He lifted the car with the jack but before he could unscrew the nuts with the wrench, Cas intervened.

“Your shoulder might be still injured, allow me”.

“No, it’s really not an issue Cas”.

“Please Dean, I won’t allow you to injure yourself further. You may be a mechanic but, I am well equipped to changing tires”.

Not wanting to object further, Dean passed the wrench over to Cas and allowed him to change the tire.

“Thank you” Dean said.

“It’s really not an issue” replied Cas.

Dean smiled, he appreciated Cas’ intervention as he never had someone help him out like this.

“I guess you help your patients until the very end, huh?”

Cas chuckled “I guess it’s what I was always meant to do” he paused, and Dean could see Cas’ features growing solemn “My mother had an illness that wasn’t properly documented, meaning that any hypothetical treatment was not based on sufficient scientific research . The common consensus was that if she had a child the illness would be cured. Of course, she took that chance and she gave birth to me. I was born on a Thursday and she named me after the angel of that day. I was born to cure her, but I never did. For ten years she suffered through the illness and I did everything I could to heal her but, being a child, I could never do that. She died when I was eleven and I made a vow that I would be a doctor and help as many people I could”.

For the first few minutes, Dean didn’t say anything as he tried to process everything Cas had told him.

“I am so sorry, Cas” he finally managed to say.

“Don’t be, she was the reason why I became the person I am today”.

Cas finished fixing the tire and, after he put all the tools back, went beside Dean to look at the stars.

“They’re beautiful, aren’t they?” said Dean.

“They are” replied Cas “They make you realize how small you are and how nothing is really under your control”.

Sam contemplated Cas’ words and looked up at the stars alongside Cas and Dean. He saw the home he left all those eons ago and realized how insignificant he was to the grander scheme of things.

_You cannot evoke love by pushing two people together._

He realized only then just how true Gabriel’s words really were. He turned his head towards Gabriel, who was looking at the stars alongside everyone else, and without thinking took his hand.

Gabriel looked down at Sam’s hand that wrapped around his and smiled. He intertwined their fingers together and leaned his head against Sam’s arm.

Sam wouldn’t admit that Gabriel was right.

Not yet at least.

**Notes for the Chapter:**

> For those who were wondering, the painting I was referring to was "The Scream"


	5. Not a typical horror setting

The men went back on the road after their stargazing session which lasted for about a half an hour. Now back in the car, each participant of this wager could reflect upon the thoughts that circled around their minds during that time.

Cas regretted not holding Dean’s hand during that moment, it was the perfect time too. Two individuals who shared a moment of intimacy through tragic backstories and long, silent observations upon the world was something Cas could only imagine happening during one of his failed tinder dates.

Sam regretted not giving Gabriel a proper apology, just to hold his pride.

Gabriel was saddened by Sam’s constant refusal to express certain emotions.

And Dean, Dean thought the stars were pretty.

The events that happened in the motel was made aware by the failed attempts to sleep on the side of the road because of the police officers who would miraculously show up out of the blue and tell them to keep driving and Dean, being a citizen of the law, would comply. The nearest motel was a six-hour drive and it was already midnight. Under regular circumstances, Dean could drive without a day of sleep however, Cas’ soft snoring beside him was somehow contagious. Even Gabriel and Sam, who don’t even need sleep, were getting drowsy.

“He’s not going to make it” said Gabriel “We need to find a building or something to call it a night before we all pass out”.

Gabriel looked over at him and could recognize Sam’s look of contemplation. Before he could ask what Sam was thinking about, Sam snapped his fingers and about a kilometer away stood an abandoned gas station.

“Why didn’t you just conjure up a nice motel?” asked Gabriel.

“You’ll see” Sam reassured.

Dean saw the gas station ahead and pulled over out of exhaustion and just pure curiosity. As a mechanic, Dean was always interested in anything related to cars, even something as tedious as an abandoned gas station would bring forward the young child inside of him. The building even had a separate garage and looked like it has two floors which only stimulated Dean’s curiosity.

Dean softly nudged the sleeping Cas and showed him the abandoned building. However, Cas did not share the same enthusiasm as Dean as his face expressed a slight discomfort.

“Tell me Gabriel, what is the link between horror movies and romance?” asked Sam.

“Absolutely nothing”.

“Wrong” Sam objected “You see Gabriel, almost every horror movie that features a romantic couple usually follows this pattern. The girl is afraid of the danger ahead whilst the man charges into the danger like a raging bull but also protects his girl with his life”.

“They also normally get only five minutes of screen time because of how dead they are before the second act” added Gabriel.

“That is not the point here” said Sam “Dean’s curiosity prevents him from feeling any fear whilst Cas is feeling nothing but fear. Because of this Cas will seek comfort from Dean by wrapping his arm around him, by leaning towards him, by snuggling with him, by kiss- “.

“It’s a gas station” Gabriel interrupted.

“It’s a _spooky_ gas station with two floors” corrected Sam.

Gabriel raised an eyebrow “What are you going to do if Cas isn’t afraid or if Dean doesn’t go inside?”.

Sam shrugged “Then I will leave it like that, I am not going to force them or anything.”

“And why is that?”.

Sam took Gabriel’s hand “Because I hate seeing you so upset” he said, surprisingly sounding sincere.

It was not the answer that Gabriel wanted but, nonetheless it was thoughtful of Sam to put someone else’s needs above his own.

“We should check it out” said Dean.

Cas looked at Dean, mildly uncomfortable “Why?”.

Dean shrugged “I don’t really know, I heard that a lot of teens do this kind of stuff and, from what I heard, they all had rather fun experiences. And, we can park the car inside the garage so no police officers can find us.”

Cas looked at the building once more and could practically see the lightning bolts crashing down. Even so, he convinced himself that he would hold his dignity (to impress Dean of course).

“Very well, let us explore the empty interior of this abandoned building”.

Dean put the car inside the small garage next to the building and hid it from view by closing the garage door, which he was surprised still worked. They entered through the side door and stepped inside. To Dean’s disappointment and Cas’ relief, there was nothing in the interior besides some graffiti art and small rocks combined with the debris. Gabriel was surprised that Sam didn’t decorate the interior with cult circles or engraved warnings on the walls.

However, his suspicions were interrupted when Sam picked up a rock and tossed it on the side of the wall. The noise caused Cas to lose his dignity and wrap his hands around Dean’s arm.

“What was that?” asked Cas, still clinging on to Dean like a squid.

Dean looked around, not bothered by Cas’ clinginess, and said “It’s probably nothing”.

Dean saw the stairs leading to the second floor and went to see with Cas walking right next to him, hands still wrapped around Dean’s arm. 

The stairs themselves felt disorientating to look at. They moved in an upward zigzag motion and appeared as though they lead nowhere despite the exterior of the building proving otherwise. It was the kind of stairs that would exist in Alfred Hitchcock’s universe of suspense and discomfort as demonstrated by Cas’ urge to grip Dean’s arm tighter when they started climbing up.

Each step was accompanied with loud creaks caused by the aging wood. The noise caused by Sam earlier only increased Cas’ misguided senses of an unwanted presence as he faced only forward and never stopped walking up, in fear that if he would turn around he would see something truly horrifying or hear it by stopping in the middle of the staircase only to hear the loud creaks still echoing across the stairway.

He leaned closer to Dean by having his head pressed on Dean shoulder and Sam, whose theories were somehow proven right, literally pointed out Cas’ actions with his index finger to Gabriel, who responded with an awkward smile and two thumbs up.

They made it to the second floor and entered another empty room except this one had a metal closet perched against the wall.

A slight discomfort was felt even by Sam, who couldn’t remember conjuring up the closet along with the building. He nudged Gabriel to indicate that something was amiss and that they should find a way to get their couple out of the building.

However, Dean, who was not prone to wise decisions, stepped forward and inched his way towards the closet. Cas started to tremble while still clinging on to Dean and Gabriel had his arms around Sam’s waist.

A certain dreaded anticipation came when Dean slowly reached for the handle. Once his hand was gripped around it, he mouthed to Cas: one, two, three.

By the third count, he quickly opened the closet door and a single mouse scurried from the closet which, combined with increasing fear that was now released, was enough for everyone to shriek in terror. Cas and Dean hugged each other for dear life while Gabriel had his entire body wrapped around Sam’s head.

Gabriel and Sam literally flew out of the building while Dean and Cas ran down the stairs and into the garage, where they flung themselves into the car and locked the doors. They clung to each other in the backseat, still trembling from the events that just took place.

Twenty minutes later, Gabriel and Sam came back from wherever they blasted themselves off to and found Cas and Dean sleeping next to each other in the backseat of the Impala.

It wasn’t exactly the one bed scenario that Sam had wanted but, it was still as effective. He smirked at Gabriel, who still did not look convinced.

There was still six days left of the bet after all, who knows what could still happen.


	6. Not a typical bake off.

It was safe to say that Cas woke up feeling quite disappointed, he expected to wake up in Dean’s arms but instead he woke up laying alone in the backseat of the Impala while Dean was driving. Cas took all the space of the backseat during his slumber which forced Sam and Gabriel to sit on the passenger seat with Gabriel sitting on Sam’s lap.

“We will soon arrive in Springfield, Illinois. We can stop at a diner to get breakfast, if you want” said Dean after he noticed that Cas was awake.

Cas yawned before he rubbed his eye “I would like that, thank you”.

Cas looked down at his wristwatch.

It was just passed eight.

Dean must’ve woken up early just to get on the road again, it was generous considering the reason behind their little road trip.

While sitting on Sam’s lap, Gabriel looked down at the map to follow Dean’s process on the road. From what Sam and Gabriel had overheard, Dean was heading to Detroit and was taking the route through Missouri and Illinois from their home in Kansas.

“How about we make a stop in Chicago?” asked Gabriel.

“That will make the trip longer and besides it isn’t me that is driving the car” reminded Sam.

Gabriel rolled his eyes “Oh come on, I’m pretty sure you can make Dean take a wrong turn”.

“Why do you want to go to Chicago anyways?” asked Sam, ignoring Gabriel’s remark.

“Because what else are we supposed to do besides driving” Gabriel whined “And besides how are you going to create an intimate moment inside a car?” he added.

“I did last night” Sam reminded Gabriel.

Gabriel scoffed “Okay Cupid, your call”.

They arrived at the diner shortly thereafter, Gabriel and Sam took off their “invisibility cloaks” five minutes after Cas and Dean got in. Sam conjured up a piece of paper and a pen to write down potential scenarios that he could inject.

“Are you having a writer’s block Anaïs Nin?” asked Gabriel when Sam didn’t write something down for the past ten minutes.

“You were right that it’s hard to create intimacy in a car” admitted Sam.

“Then why don’t you invoke a city trip or something, instead of trying to keep them in the car?”. 

“But what if something happens? What if they don’t like it? Or What if Dean sees a pretty girl and leaves Cas behind?”.

_I needed them to stay together because the minute one of them leaves it wouldn’t work anymore._

Gabriel, who finally realized Sam’s motivations for keeping Cas and Dean inseparable in the car, leaned forward “Sam, they’re not going to tear apart that easily, especially when Dean made a promise to Cas to take him to the car shop in Detroit. And besides” he took Sam’s hand “Don’t you think that a relationship means more if it can persist even when the couple is apart?”.

_Then why was it not the case for us?_ Sam wanted to say but decided not to. Instead he stood up and went to the nearest bathroom. Before Gabriel could question what Sam was doing, Sam came back. Gabriel quickly noticed that Sam was no longer wearing his pristine suit but rather a pair of plain jeans and flannel. When Sam was walking towards Cas and Dean’s table, he realized what was going on and quickly followed Sam’s plan.

“Okay if we go along this direction, we will be in Detroit at four pm at the earliest” said Dean, showing the map to Cas.

“Oh, that’s is wonderful! You two are going to Chicago?” asked Sam, interrupting Cas and Dean’s conversation.

“Well, we are going the general direction” confirmed Dean.

“That’s perfect! You have no idea how convenient this is for my boyfriend and I” said Sam, trying his absolute best to put up an enthusiastic performance even though it fell flat.

“Gabe!” Sam called when he saw Gabriel exit the bathroom with a dark green jacket, red shirt, and jeans “These two are heading to Chicago”.

“Really?” said Gabriel, putting an equally bad performance as Sam “This is just dandy”.

“You see, Gabe and I were travelling on a bus tour to Chicago, but we missed the bus” explained Sam when Dean and Cas gave them a confused, and slightly uncomfortable, look.

“We are such Dodo’s” added Gabriel, completely immersed into his theatrical performance. 

“That’s just horrible” said Cas who was honestly not paying any attention to the exaggerated performances “Dean we should help them”.

“I don’t know, Cas. We are going the general direction but, it’s not like we will be passing the city. It will be a big detour for us”.

Sam put on his best pouty face “It’s okay, we understand. Come on, Gabe maybe we can find someone else to take us to that _pie_ bakery with _excellent reviews_ ” he said, placing a large emphasis on the pie and excellent reviews.

Surely enough, when Gabriel and Sam turned around and started walking away, Dean intervened.

“Wait! I think Cas and I can afford a small detour”

Cas smiled and nodded in agreement.

Gabriel and Sam gave each other a small smirk.

“That’s excellent!” they both exclaimed.

***

_Isn’t this technically cheating?_ Asked Gabriel telepathically.

_If I don’t literally manipulate their minds then it’s fine, and besides we didn’t say that we always had to be in the background._ Answered Sam.

_I guess so, but how are you going to conjure up an entire bakery?_

_You’ll see._

“So, where did you two first meet?” asked Cas when Dean started driving.

“Oh, we met in Bethlehem” responded Gabriel.

“Wow, that’s amazing” exclaimed Cas “And how did you fall in love?”.

There was a short pause.

“It was love at first sight” replied Sam after a moment with not an ounce of mockery or insincerity in his voice.

It was the time to speak the truth, especially now that someone had finally asked about the state of their relationship. The uncertainty of Gabriel’s affection towards Sam over the centuries had become burdensome, even in some occasions, aggravating. For centuries Sam had to push back the simple question concerning Gabriel’s affection, simply because he feared the response that could be offered.

Now that the question was finally asked, there was nothing hindering the confession.

“I proposed a fun little wager just to get things started. I intentionally gave him the victory in the hopes that he would stick around which he inevitably did. Our time together were always in short periods and they would never feature rom-com movie. I was never sure if he loved me back considering the lack of romantic intimacy in those moments. I figured if he didn’t love me the moment we met; he wouldn’t love me at all.”

Sam’s features grew solemn. He didn’t dare to meet Gabriel’s eyes in fear that he would look dejected if he did. He realized that he didn’t answer Cas’ question and he should have felt embarrassed however, that feeling was subsided by the feeling of lost time trying to invoke a seemingly condemned romance.

“He was wrong, though” said Gabriel, he looked at Sam’s surprised expression for a moment before continuing “When Sam introduced himself and made that wager I admit that I was cautious however overtime I have come to realize the motive behind his actions and began to speculate on the possibility of becoming more intimate. Those moments may have not been explicitly romantic, but they were nevertheless important because they were sincere. It took time to get to this point where we are now.”

_You cannot evoke love by pushing two people together._

“And fortunately for him I could wait.” Finished Sam.

“You two are so sweet” said Cas, completely ruining their moment and looked like he could barely keep his composure “Dean, why can’t we be this cute?” he asked mockingly.

“I think we’re adorable” replied Dean.

***

“So, where is this pie restaurant you guys were talking about?” asked Dean before anybody had the opportunity to get out of the car.

“It should be around here” replied Sam.

They walked a bit further into the town with Dean leading the way despite not knowing the location of the bakery and holding Cas’ hand to make sure he didn’t fall behind. Sam and Gabriel walked in a steadier pace with Gabriel holding unto Sam’s arm and watching intently at Sam’s fingers, waiting for him to snap them and conjure up a nice building. However, Sam kept his hands in his jeans pockets and didn’t seem so worried about Dean moving farther ahead.

“How are you going to conjure up an entire building in the middle of town?” asked Gabriel.

Sam slightly smirked “I don’t have to”.

Before Gabriel could ask, Dean interrupted:

“I found it”

In front of them stood the biggest bakery that Gabriel has ever seen and looked like something Cupid himself would decorate as the color of bakery was pink and was embellished with heart shapes bricks.

Gabriel turned over to Sam looking quite horrified “What the heck is this”.

“Oh this, it’s a bakery that serves specifically wedding pies and, on some occasions, also do anniversary theme pies. They do this annual thing where they invite couples to bake pies completely for free”.

“And how do you know of this bakery’s existence?”.

Sam blushed “No particular reason”.

A young baker came outside through the front door and asked:

“Are you gentlemen here for the annual couple bake off?”

“Couple bake off?” asked Dean who now took his face off the window displaying the pies.

“Oh Dean, you’re so forgetful” said Sam “Didn’t I tell you that this bakery has an annual bake off where you can bake pies for _free”._

Sam didn’t tell him, he just thought it would be funny to make Dean uncomfortable.

And he was slightly uncomfortable.

“I don’t know how to bake pies though”.

“I am quite knowledgeable of the practice” objected Cas.

Sam gave an enormous grin “Well then, lets just see if you can hold that position. It’s going to be tough beating my little angel here” he nudged Gabriel and Gabriel tried to compress the blush creeping into his face.

“If you gentlemen are ready you can come inside” said the baker.

They went inside the building, which looked just as extravagant as the outside, and entered the back. Where there were six backing tables with four of them already taken by their respected couples. Both couples took the tables beside each other and watched intently at the baker who stood in front of them with her own baking table and her own significant other.

“Okay first what we want to do is mix the flour, butter, salt, sugar, and water”.

None of the couples really thought of anything when they put all the ingredients together until the baker and her significant other showed them how to compress the dough together into a small ball.

To put it bluntly, the lady and her significant other were recreating that one scene from “Ghost” where the star couple manage to make pottery seductive.

Dean gave a nervous laugh “I guess they really love ‘Ghost’ huh, Cas”.

“Why would you insinuate that they enjoy the paranormal?”.

“No Cas, I- “he sighed heavily “You know what, never mind”.

Dean looked around and realized that all the couples were following the instructions very thoroughly, even Gabriel and Sam with Sam standing very appropriately behind Gabriel and practically maneuvering his hands.

Giving into peer pressure and his desire to consume an entire pie, Dean gave in. He went behind Cas and very carefully follow the instructors’ guidance. Cas didn’t say anything as he become stiff as a wooden plank.

This way an interesting way to make pies.

By the end, Cas and Dean managed to create a blueberry pie with leave shape dough decorating the edges (because Cas was an artist that way) and Sam and Gabriel made a chocolate pie with heart shape sprinkles decorating the top (because Gabriel was adorable that way). It was getting late and initially Dean wanted to continue driving but changed his mind when Sam and Gabriel insisted that they go sleep in a hotel for the night.

Sam and Gabriel reserved a room with a king size bed (to keep their couple persona of course) and Cas and Dean took a room with two queens (because Dean still retained his “straight” persona). Later that night, both couples went to the bar downstairs and quickly noticed the karaoke machine. Dean and Gabriel took it upon themselves to go on stage and sing every song that came up. Nobody seemed to mind as Dean and Gabriel were pretty good singers and Cas and Sam looked at them fondly from their seats in the corner of the bar.

“I have to thank you for the fun time ” said Cas “For two days, Dean and I had many unusual things happen to us but, I have to say this is one of the most fun occurrences”.

“Really?” asked Sam, trying his best to hide the fact that he was the cause for most of those occurrences “Well I am glad you manage to have a great time”.

Cas smiled “I want to have more moments with him, though”.

“oh?”.

“We are going to Detroit tomorrow to purchase a new car after mine spontaneously combusted” clarified Cas “After I buy the car, I am pretty sure we will go our separate ways but before that happens, I want to share one more moment”. Cas’ features grew solemn “What do you think I should do?”.

“I can’t really tell you” replied Sam, and he couldn’t as this would be the equivalent of manipulating Cas’ mind “In the end of the day it’s your decision to make” added Sam, thinking that this answer could probably suffice.

“You and Gabe seem so happy with each other” said Cas fondly.

“I have to say it was a long process though” Sam admitted “Even now there is always room to grow”.

Dean and Gabriel finished their song and were about to begin a new one before the manager politely told them that the jazz players were getting ready for tonight’s show. It was safe to say that both men were disappointed until one of the saxophone players started playing “Careless Whisper” to get the crowd started. Gabriel’s face lit up with joy before running towards Sam and pulling his arm.

“Sammy, we got to dance to my favorite song” he exclaimed.

“Okay, okay” chuckled Sam before getting up to dance with Gabriel.

Throughout the night Sam, Gabriel, Dean, and Cas danced their hearts out and drank some beers for good measure.

By the end, all men were feeling tipsy and decided to call it a night, unaware of the fact that they inconveniently switched rooms.


	7. The end

Sam woke up feeling slightly isolated, he expected to have Gabriel sleeping next to him or at the very least snuggle up against him. They have leaned against each other on numerous occasions so Sam should know how it feels to sleep with company.

The confession made in the car had eased the tension that may have existed between them. Sam would not admit that he was growing soft, but it did give him genuine satisfaction when Gabriel was more affectionate towards Sam’s less brutish moments.

“Gabe” Sam whispered as he reached for the other side of the bed and soon realized that the edge was much closer than he had expected.

Confused he opened his eyes and saw that he was sleeping on a singular bed. He got up and quickly noted the empty bed sitting next to him. The bed’s rumbled sheets indicated that someone slept beside him and was already awake. The question of who slept on the separate bed was quickly answered when Sam saw Gabriel leaning against the wall with the bottom end of a drinking glass pressed against his ear.

“What are you doing?” questioned Sam.

“I am trying to hear the sounds of Cas and Dean’s startled shock” replied Gabriel.

“What are you talking about?”.

“We accidentally switched rooms” explained Gabriel “Which means that those two are sleeping in the same bed”.

With that revelation, Sam quickly got out of bed and placed his ear against the wall.

“I can’t hear anything”.

“Here, this might help”.

Gabriel took out a drinking glass, which he conveniently already had in hand, and gave it to Sam. 

“Thank you”

Sam and Gabriel pressed their ears against the bottom end of the drinking glass and awaited Cas and Dean’s reaction.

Soon enough a loud yelp could be heard from the opposite side of the wall. Sam and Gabriel pressed themselves closer into their hearing devices.

“I am so sorry Dean; I didn’t mean for you to sleep on the floor” It was Cas’ voice.

Gabriel and Sam could hear Dean grunting in pain. Cas couldn’t have just now push Dean off the bed as Sam and Gabriel were sure that they would hear a loud thud.

However, the alternative became soon clear.

“Did Cas push Dean of bed when they were asleep?” asked Gabriel.

Sam grunted “Of course he did”.

“I think we switched rooms with Samuel and Gabe, wait I will check” said Dean.

Sam and Gabriel instantly got up on their feet and put the glasses on their individual nightstand. They soon heard Dean knocking on their door. Sam was about to answer when Gabriel intervened:

“Wait, we got to act surprise”.

“Crap you’re right”.

“Oh, wow would you look at that” exclaimed Sam with an exaggerated expression of surprise “It appears as though we switched room”.

Sam then opened the door and was quite surprised by Dean’s rather monotone expression, at this point he had gotten used to all the shenanigans that he had endured this past three days. Sam and Gabriel apologized profusely but, again Dean really didn’t seem to mind. Everybody got ready just before noon and decided to say their goodbyes by the entrance of the hotel. Of course, Sam and Gabriel were just going to sit unnoticed on the backseats of the Impala but, it was a teary farewell, nonetheless. Gabriel and Dean shared the memories of their karaoke night while Sam and Cas gave each other a simply, yet affectionate hug.

After 4 hours of driving, they finally made it to Detroit. Dean took Cas to the car shop almost immediately and started searching for Cas’ new vehicle. Cas made sure to avoid any car that bore any resemblance to his old one, in the fear that one would spontaneously go up in flames. Sam thought about blowing one up just for laughs however, one look at Gabriel’s bitchface was enough for him to reconsider.

Things were going well as, thanks to Dean’s guidance, Cas managed to find a car that he thought would suit his needs. Before he could purchase it though, a stranger approached them and seemed to recognize Dean because he said:

“Dean, l didn’t know you were in Detroit”.

“Hey Benny, I’m just here to make a purchase with a friend” replied Dean.

“Definitely looks like it” said Benny before giving Dean a hug which Dean gladly accepted “So what are you buying?”.

“A Lincoln Continental Mark V” replied Cas “I am trying something new since my last car went up in flames”.

Benny gave Dean an alarmed look.

“It’s a long story” informed Dean.

“Well, since you’re here; Dean I was wondering if you could help me with this project I’m doing”.

“What’s the project?” asked Dean.

“I am restoring a Duesenberg J from scratch. I am sure with your help we can get it working in a month”.

Cas looked over at Dean and could see that he was genuinely intrigued.

“I would love to Benny but, I- “

Dean cut himself of and gestured towards Cas.

“Don’t be preposterous, Dean” objected Cas “You should engage upon this project. I know the way back so there is no need to dread upon the possibility of me getting lost”.

Dean smiled at Cas before taking Benny’s offer.

“It’s settled then” said Benny and Sam simultaneously.

Gabriel looked over at Sam and found himself on the day of the Crucifixion where Sam had lost. The expression he bore was one of accepted defeat except this time he didn’t take it so proudly.

“You win Gabriel” Sam offered his hand which Gabriel hesitantly accepted “I can’t make them fall in love four days if they’re not going to see each other for a month, right?”.

Before he could reply, Gabriel limply allowed Sam to shake his hand to approve Sam’s defeat.

“Right” Gabriel muttered.

Sam let go of Gabriel’s hand and with a saddened smile said “Take care, Gabriel” before flying off and leaving Gabriel behind. 

“Dean” said Cas after Benny left “Before I go, would you want to go somewhere?”

Gabriel was momentarily interrupted from his dejection when Dean replied “Sure, what do you want to do?”.

After purchasing his car, Cas and Dean went to a Festival celebrating the fourth of July. The festival brought with it a large Ferris wheel, which Cas was more then eager to ride on.

Gabriel, who was still following them despite the bet being forfeited, took the cabin behind them and watched the festival from below. Through telepathy he realized that Cas and Dean had not uttered a word to each other. One would expect then that things were going poorly however, Gabriel recognized that this was a different kind of silence, one that was not based upon awkward tension but rather based upon a certain fondness felt only by companions (and potential lovers). 

Gabriel smiled to himself when he realized just how well things were going for them.

“What are you thinking about”. 

Gabriel nearly screamed at Sam’s sudden intrusion. With a hand placed on his chest he yelled:

“What in the heck is the matter with you?!”.

“I came here to give you these”

From behind his back Sam pulled out a bouquet of White Lilies and offered it to Gabriel.

“You are not pining over me, are you?” Sam asked flirtatiously.

Gabriel scoffed “As if” but he gladly accepted the lilies.

“Why are you here? Wait don’t tell me” Sam interrupted before Gabriel had the chance to open his mouth “You are here to see the fireworks, but I don’t see any”.

“They only start in two hours”.

“Well that won’t do” objected Sam.

With a snap of his fingers, Sam put on a firework display.

Gabriel scoffed “Don’t be like this, I know exactly why you left”.

Sam looked down in disappointment, he knew he shouldn’t put up such a mediocre performance in front of Gabriel.

“I just wish I wasn’t so hasty in the beginning. I should have let them come together in their own pace instead of forcing them to stay together and blowing up Cas’ car. I would have lost the bet anyways but, at least it wouldn’t have felt like such a defeat”.

Gabriel smiled “I don’t think your giving yourself enough credit ”.

“What makes you say that?”

Gabriel didn’t answer, instead he waited until they were out of the cabin. Once out, Sam saw Dean and Cas walking together and asked:

“Why are those two here?”.

“Cas wanted to bring Dean here before he left” replied Gabriel “I have to say the love feels more real when it comes from them.”

Gabriel smiled softly “I am sure that their relationship will continue to grow despite not seeing each other for other a month.” He then turned his attention towards Sam “If you want, we can continue the wager. You have four days after all”.

Sam considered the offer, for a minute he thought he would oblige and snap his fingers but instead, he simply put his hands in his pockets.

“Let’s give them more time”.

**Notes for the Chapter:**

> All good things must come to an end, right?
> 
> I might write a one shot sequel to this story, but i haven't decided yet. 
> 
> Again, thank you to everyone who took the time to read my work! you guys are awesome!


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